The casual visitor to Boston’s South End might stop by for brunch, take in an event at the Cyclorama, or give the neighborhood’s distinguished Victorian brownstones a quick glance. But why not stay overnight and really get up close and personal with the area?

Here’s my itinerary for the South End, and feel free to mix things up as you find necessary. Remember: there’s always time to come back again.

Bed, Breakfast, & Bernstein

In an era awash with generic and sterile environments to lay your head down, the Encore B&B is the perfect antidote for the informed traveler. Located on the peaceful climes of West Newton Street, this bed & breakfast is a culture lover’s paradise. Your hosts are Reinhold and David, and they are both splendid resources for learning more about the South End and its many charms. The rooms, you ask? Fashioned as tributes to such luminaries as Stephen Sondheim, Edward Albee, and of course, Leonard Bernstein (son of Brookline, Mass, or didn’t you know already?)

Each room has the usual fine touches one might expect, including tastefully modest televisions, exposed brick walls, comfortable beds, and of course, posters and books that reference each of the cultural masters the rooms are named after. It’s the perfect level of comfort and familiarity. It’s a great headquarters for your South End sojourn and yes, they do also offer a nice breakfast with robust coffee.

Arts & Culture Amidst the Brownstones

After a leisurely breakfast, you will walk up Tremont Street and encounter a building that seems a bit out of place. What is this curiosity, this domed wonder, you ask? It’s the Cyclorama, just an august structure built to house a remarkable painting of the Battle of Gettysburg back in 1884. Today it is operated by the Boston Center for the Arts, and visitors can come in and check out a rotating series of exhibits, take in a show (the celebrated Bread & Puppet theater group is a favorite), or stop on by the nearby Beehive for some late night jazz.

Some coffee, perhaps a pastry?

After an afternoon of walking around the South End, considering its architecture, stopping by the Cyclorama, you may need require a moment of respite. Stop on by the South End Buttery over on Shawmut Avenue to share a sandwich, have a cappuccino, or sit in the comfortable and comely back room to have a glass of wine. My personal favorites here are the range of cupcakes named after owner Richard Gordon’s dogs (try the Dexter German Chocolate cupcake for starters).

Open the Door, Feel the Warmth

On a warm day, Toro will cool you. On a cold day, Toro will warm you. Yes, their tapas are well known in all quarters of Boston and beyond, but it is the congeniality of the place that I find most welcoming. When you walk in the door it is camaraderie that is apparent from the individual pouring your water to the bartender talking with a first-time visitor about what type of wine the evening requires.

Toro, credit: Hilary O’Rourke

What do I recommend? I’d love to just throw out the boilerplate answer of “Everything”. That’s too easy; the lazy man’s throw away reply. I’d start out with some Aceitunas (marinated olives in bay leaf, orange and spices), and the Atun tartare, which is brought alive with coconut milk, lime, mint, and cilantro.

Order a beverage, repose, and then proceed to put in an order for their stellar paella de Zanahoria. It takes about 20-30 minutes to prepare, but do you really want to leave sooner rather than later? You’ll want to wait as this lovely variation on this standard includes turnips, carrots, sunchokes, spinach and Calasparra rice.

As for the tapas? Make sure and try the Coles de Bruselas a la plancha (brussels in the minimalist manner with olive oil and sea salt) and the Croquettas de Bacalao (salt cod fritters with lemon rings and aioli)

After you’re done with dinner, maybe you can find room at the bar. Walk on over and have another glass of wine for me. And for you, of course.

Jazz Since 1947, Served All Night Long

On the first floor of one of the hundreds of brownstones in the South End, you will hear jazz seven nights a week, 365 days a year. Wally’s Cafe is just a short walk from Toro on Massachusetts Avenue and it is the place that many casual visitors might not give a second look. It is the last of the truly old school jazz haunts in Boston. The spirit is always willing here and musicians from nearby Berklee College of Music hold court here from 9pm to around 1am, joined by a caravansary of other musicians, young and old. Wally’s doesn’t have a cover, but you’ll want to come early to grab a seat.

After all of this drinking, this eating, and this music appreciation, get on back to the Encore for some rest. After all, there’s breakfast to be had in the morning and more exploring to be done.

Max Grinnell is a writer based in Cambridge, MA, who writes about cities, public art, geography, travel, and anything else that strikes his fancy. His writings can be found online at www.theurbanologist.com and he tweets over @theurbanologist.

Taylor Trinque is an artist studying at the Massachusetts College of Art and Design. A native of Rhode Island, Taylor finds inspiration in the world of the color wheel and the expressive works of the Impressionists. You can see more of her work here: http://artbytaylor.tumblr.com/